Dual Photoredox/Copper-Catalyzed Three-Component Alkylcyanation of Alkenes and 1,4-Alkylcyanation of 1,3-Enynes Employing Sulfoxonium Ylides as the Carbon Radical Precursors DOI
Zixuan Yang,

Xue‐Cen Xu,

Bowen He

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 3, 2024

A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl from sulfoxonium ylides adds to carbon-carbon double bonds styrenes or 1,3-enynes, generated benzylic allenyl radicals couple with a Cu(II) cyanide complex achieve selective cyanation. The reaction exhibits high chemo- regioselectivity wide substrate scope, providing an efficient method for synthesis nitriles in single step.

Язык: Английский

Visible light promoted synthesis of allenes DOI
Jitender Singh,

Barakha Saxena,

Anuj Sharma

и другие.

Catalysis Science & Technology, Год журнала: 2024, Номер 14(18), С. 5143 - 5160

Опубликована: Янв. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Язык: Английский

Процитировано

3

Metallaphotoredox Synthesis of Axially Chiral Tetrasubstituted Allenes through Regio- and Enantioselective 1,4-Carbocyanation of 1,3-Enynes DOI

Keyi Peng,

Ya-Sheng Cao,

Quanyuan Wang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(18), С. 14048 - 14057

Опубликована: Сен. 10, 2024

Язык: Английский

Процитировано

3

Nickel-Catalyzed Reductive 1,4-Alkylacylation of 1,3-Enynes Enabling Synthesis of Allenyl Ketones DOI

Quanyuan Wang,

Keyi Peng,

Xupei Yao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

A nickel-catalyzed reductive 1,4-alkylacylation of 1,3-enynes has been established using nonactivated tertiary alkyl bromides and aromatic anhydrides as dual electrophiles. This protocol enables efficient assembly tetrasubstituted allenyl ketones with high chemo- regioselectivity. Mechanistic insights reveal the radical relay process involving synergistic interactions nickel zinc. The ketone products serve modular building blocks, particularly for constructing fully carbon-substituted furans via Au-catalyzed cycloisomerization selective 1,2-aryl migration, enhancing synthetic practicality.

Язык: Английский

Процитировано

0

Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access allenes and dienes DOI Creative Commons

Zhuomin Chi,

Yongchao Zhou,

Bingbing Liu

и другие.

Chemical Science, Год журнала: 2024, Номер 15(33), С. 13271 - 13278

Опубликована: Янв. 1, 2024

The radical-mediated difunctionalization of 1,3-enynes facilitates rapid access to structurally diverse allenes and dienes.

Язык: Английский

Процитировано

2

Ball-Milling-Enabled Nickel-Catalyzed Reductive 1,4-Alkylarylation of 1,3-Enynes under an Air Atmosphere DOI
Lei Hao, Bobo Wang, Yufang Yang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7688 - 7694

Опубликована: Авг. 29, 2024

A ball-mill-enabled nickel-catalyzed 1,4-alkylarylation of 1,3-enynes with organic bromides has been developed, offering a versatile method for assembling tetrasubstituted allenes. This approach, the first ball-milling-based remote radical coupling, overcomes limitations traditional solution-phase methods, such as need air- and moisture-sensitive reagents, use bulk solvents, prolonged reaction times. Given outstanding performance reduction coupling reactions, we anticipate further advancements in sustainable efficient synthetic methodologies.

Язык: Английский

Процитировано

2

Photoreductive 1,4-Dicarbofunctionalization of 1,3-Enynes with Organoiodides and Cyanoarenes via Halogen-Atom Transfer DOI

Liangfeng Yang,

Liang Zeng,

Yilin Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7661 - 7666

Опубликована: Авг. 28, 2024

A photoreductive halogen-atom transfer (XAT) strategy for 1,4-dicarbofunctionalization of 1,3-enynes with organoiodides and cyanoarenes is disclosed, enabling access to functionalized allenes in a highly regio-, chemo-, stereoselective manner. Upon the photoredox catalysis activation Et

Язык: Английский

Процитировано

1

Palladium-catalyzed four-component domino sulfonylation and carbonylation of 1,3-enynes at room temperature DOI
Jing Wang, Jun Ying

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5851 - 5858

Опубликована: Янв. 1, 2024

A novel palladium-catalyzed four-component domino sulfonylation and carbonylation of 1,3-enynes has been developed, which enables the rapid incorporation allene, sulfone, carbonyl amine units into one single molecule simultaneously.

Язык: Английский

Процитировано

1

Dual Photoredox/Copper-Catalyzed Three-Component Alkylcyanation of Alkenes and 1,4-Alkylcyanation of 1,3-Enynes Employing Sulfoxonium Ylides as the Carbon Radical Precursors DOI
Zixuan Yang,

Xue‐Cen Xu,

Bowen He

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 3, 2024

A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl from sulfoxonium ylides adds to carbon-carbon double bonds styrenes or 1,3-enynes, generated benzylic allenyl radicals couple with a Cu(II) cyanide complex achieve selective cyanation. The reaction exhibits high chemo- regioselectivity wide substrate scope, providing an efficient method for synthesis nitriles in single step.

Язык: Английский

Процитировано

1